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Gilpin was born in Cumberland, the son of Captain John Bernard Gilpin, a soldier and amateur artist. From an early age he was an enthusiastic sketcher and collector of prints, but while his brother Sawrey Gilpin became a professional painter, William opted for a career in the church, graduating from Queen's College, Oxford in 1748.

While still at Oxford, Gilpin anonymously published A Dialogue upon the Gardens ... at Stow in Buckinghamshire (1748). Part guidebook to Stowe, part essay on aesthetics, this shows that Gilpin had already begun to develop his ideas on the picturesque. Unusually for the time, Gilpin showed an appreciation of wild and rugged mountain scenery, perhaps rooted in his Cumbrian upbringing; even more unusually, he expressed ideas about the perception of beauty which were purely aesthetic and often divorced from other qualities of the object viewed, such as morality or utility.

After working as curate, Gilpin became master, and from 1755 headmaster, at Cheam School. He was an enlightened educationist, instituting a system of fines rather than corporal punishment and encouraging the boys to keep gardens and in-school shops. His broad intention was to promote "uprightness and utility" and give his pupils "a miniature of the world they were afterwards to enter."[2] Gilpin stayed at Cheam until 1777 when he moved, with his wife Margaret, to become Vicar of Boldre in the New Forest in Hampshire. While there he took as a child pupil the future poet Caroline Anne Bowles. Another pupil was his nephew, the painter William Sawrey Gilpin. He was succeeded at Cheam by his son, another William Gilpin.

William Gilpin died at Boldre, Hampshire, on 5 April 1804 and was buried there on 13 April. He was survived by his wife, Margaret (1725–14 July 1807), to whom he was married for over 50 years.[3] His older son, John Bernard, became British consul for Rhode Island. His younger, William, had taken over at Cheam School. His two daughters predeceased him.[1]

In 1768 Gilpin published his popular Essay on Prints where he defined the picturesque as '"that kind of beauty which is agreeable in a picture" and began to expound his "principles of picturesque beauty", based largely on his knowledge of landscapepainting. During the late 1760s and 1770s Gilpin travelled extensively in the summer holidays and applied these principles to the landscapes he saw, committing his thoughts and spontaneous sketches to notebooks.

Gilpin's tour journals circulated in manuscript to friends, such as the poet William Mason, and a wider circle including Thomas Gray, Horace Walpole and King George III. In 1782, at the instigation of Mason, Gilpin published Observations on the River Wye and several parts of South Wales, etc. relative chiefly to Picturesque Beauty; made in the summer of the year 1770 (London 1782). This was illustrated with plates based on Gilpin's sketches, etched by his nephew William Sawrey Gilpin using the new aquatint process. There followed Observations on the Lake District and the West of England and, after his move to Boldre Remarks on Forest Scenery, and other woodland Views ... (London 1791).

Gilpin's watercolour technique has been compared to that of Alexander Cozens.[5] Both texture and composition were important in a "correctly picturesque" scene. The texture should be "rough", "intricate", "varied", or "broken", without obvious straight lines. The composition should work as a unified whole, incorporating several elements: a dark "foreground" with a "front screen" or "side screens", a brighter middle "distance", and at least one further, less distinctly depicted, "distance". A ruined abbey or castle would add "consequence". A low viewpoint, which tended to emphasise the "sublime", was always preferable to a prospect from on high. While Gilpin allowed that nature was good at producing textures and colours, it was rarely capable of creating the perfect composition. Some extra help from the artist, perhaps in the form of a carefully placed tree, was usually required.

In contrast to other contemporary travel writers, such as Thomas Pennant, Gilpin included little history, and few facts or anecdotes. Even Gilpin's descriptions can seem quite vague, concentrating on how scenery conformed to picturesque principles rather than its specific character. In one much-quoted passage, Gilpin takes things to an extreme, suggesting that "a mallet judiciously used" might render the insufficiently ruinous gable of Tintern Abbey more picturesque. In the same work he criticises John Dyer's description of the view from Grongar Hill for describing a distant object in too much detail. Such passages were easy pickings for satirists such as Jane Austen demonstrated in Northanger Abbey as well as many of her other novels and works. (Elizabeth Bennet, in Pride and Prejudice, notably refuses to join Mr. Darcy and the Bingley sisters in a stroll with the teasing observation, "You are charmingly group'd, and...The picturesque would be spoilt by admitting a fourth.")

Although he came in for criticism, Gilpin had published at exactly the right time. Improved road communications and travel restrictions on continental Europe saw an explosion of British domestic tourism in the 1780s and 1790s. Many of these picturesque tourists were intent on sketching, or at least discussing what they saw in terms of landscape painting. Gilpin's works were the ideal companions for this new generation of travellers; they were written specifically for that market and never intended as comprehensive travel guides.

Although Gilpin sometimes commented on designed landscapes, for him the picturesque was always essentially just a set of rules for depicting nature. It was left to others, most notably Richard Payne Knight, Uvedale Price and Thomas Johnes, to develop Gilpin's ideas into more comprehensive theories of the picturesque and apply these more generally to landscape design and architecture. Ultimately, these grand theories of wild natural beauty gave way to the tamer and more commercialised picturesque of the mid 19th century. But Gilpin's works remained popular and several new editions, with additions by John Heaviside Clark, were brought out.

Gilpin also lives on as the model for the satirist William Combe's clever but cruel Tour of Dr Syntax in Search of the Picturesque (1809), brilliantly illustrated by Thomas Rowlandson. This poor curate sets off on his straggly mare Grizzle in a quest for picturesque scenery, often (and usually to his discomfort) oblivious to the realities of the world around him.

As well as his picturesque writing, Gilpin published numerous works on moral and religious subjects, including biographies of Hugh Latimer, Thomas Cranmer and John Wicliff. A proportion of the profit from his writing went on good works in his parish, including the endowment of the school at Boldre which now bears his name. Many of the manuscripts of his tours, including unpublished or only recently published material, are now housed in the Bodleian Library, Oxford.

Dialogue upon the gardens of the Right Honourable the Lord Viscount Cobham, at Stow in Buckinghamshire (1748)

An essay on prints: containing remarks upon the principles of picturesque beauty; the different kinds of prints; and the characters of the most noted masters (1768)

Observations on the River Wye, and several parts of South Wales, etc. relative chiefly to picturesque beauty; made in the summer of the year 1770 (1782)

Observations, relative chiefly to picturesque beauty, made in the year 1772, on several parts of England; particularly the mountains, and lakes of Cumberland, and Westmoreland (1786)

Observations, relative chiefly to picturesque beauty, made in the year 1776, on several parts of Great Britain; particularly the High-lands of Scotland (1789)

Remarks on forest scenery, and other woodland views (relative chiefly to picturesque beauty), illustrated by the scenes of New Forest in Hampshire (1791)

Three essays: on picturesque beauty; on picturesque travel; and on sketching landscape: to which is added a poem, On landscape painting (1792)

Observations on the Western parts of England, relative chiefly to picturesque beauty; to which are added a few remarks on the picturesque beauties of the Isle of Wight (1798)

Observations on the coasts of Hampshire, Sussex, and Kent, relative chiefly to picturesque beauty, relative to Picturesque Beauty, made in the Summer of the year 1774 (1804)

Two essays: one on the author's mode of executing rough sketches; the other on the principles on which they are composed. To these are added, three plates of figures by S. Gilpin (1804)

Observations on several parts of the counties of Cambridge, Norfolk, Suffolk, and Essex. Also on several parts of North Wales, relative to picturesque beauty in two tours, the former made in ... 1769, the latter in ... 1773 (1809)

The life of Bernard Gilpin: collected from his life written by George Carleton, bishop of Chichester, from other printed accounts of the times he lived in, from original letters, and other authentic records (1752)

The life of Hugh Latimer, Bishop of Worcester (1755)

The lives of John Wicliff; and of the most eminent of his disciples; Lord Cobham, John Huss, Jerome of Prague, and Zisca (1765)